We do not stay overnight in Whitehorse. (Thanks for the correction.) We arrive in Anchorage and then leave the next day via rail to Denali, where we spend two nights. We then bus to Fairbanks for one night where I hope to see the Northern Lights, and then fly to Dawson for two nights. We fly to Whitehorse (but do not spend the night), and then take the train from Whitehorse to Skagway and get on the ship that same day. Supposedly we have a couple of hours in Skagway if we don't choose to board the ship right away. I would rather explore Skagway a bit before boarding. They just don't give us a lot of detail about timing, and since none of these Yukon excursions are offered this year, there is not much information I can find.
I am thinking of arriving a day early in Anchorage to do some hiking or book an excursion of some type there, since the flight from Chicago will take most of a whole day. We may also spend a day on the back end in Vancouver or Seattle, so we will have some time to explore that area.
I have plenty of time to work out those details... unfortunately, I am limited to only two weeks off from work. This tour leaves on a Wednesday and ends on a Saturday, but it does also have a stop in Ketchikan, which would be another opportunity for us to do some exploring.
Thanks again for any recommendations you have!